Cyclopentylamine → HCID 10662002, compound

HRID 1954720Notes

Reaction equation

Cl[C:2]1[C:3]2[N:4]([C:13]([CH3:16])=[CH:14][N:15]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[C:7]([Cl:12])[CH:6]=2.[CH:17]1([NH2:22])[CH2:21][CH2:20][CH2:19][CH2:18]1>>[CH:17]1([NH:22][C:2]2[C:3]3[N:4]([C:13]([CH3:16])=[CH:14][N:15]=3)[C:5]3[C:10]([N:11]=2)=[CH:9][CH:8]=[C:7]([Cl:12])[CH:6]=3)[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

Reactant 2

HCID 2906Cyclopentylamine

HCID 53747984HCID 53747984, compound

Product 1

HCID 10662002HCID 10662002, compound

Procedure

By reaction of 2,3,6-trichloroquinoxaline with propargylamine, following a procedure that is similar to that described in example 2, there is obtained 8-chloro-1-methylimidazo[1,2-a]quinoxaline-4(5H)-one (m.p. >300° C.) and, subsequently, 4,8-dichloro-1-methylimidazo[1,2-a] quinoxaline. By reacting this product with cyclopentylamine according to the method described in example 3, there is obtained 4-cyclopentylamino-8chloro-1-methylimidazo[1,2-a]quinoxaline. m.p. (DSC)=130.5° C.(onset); IR (KBr): 3421, 2954, 1555 cm-1 ; 1H-NMR (CDCl3): δ7.95 (1H,d, J=2 Hz), 7.6 (1H,d, J=9 Hz), 7.35÷7.15 (2H,m), 6.1 (1H,d), 4.5 (1H,s), 2.8 (3H,s), 2.4÷2.05 (4H,m), 2.0÷1.3 (4H,m); UV (EtOH): λmax =227, 251, 276, 305, 336 nm. Elementary analysis for C16H17ClN4 (m.w. 300.79): calcd. C 63.89, H 5.70, N 18.63%; found C 63.79, H 5.79, N 18.58%.

Sources & evidence

ORD record: ord-ebf29998610245a6919510e583822c32
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06124287

Reaction notes

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